WO1981002423A1 - Moyens de coloration et procede pour la coloration de fibres cellulosiques - Google Patents

Moyens de coloration et procede pour la coloration de fibres cellulosiques Download PDF

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Publication number
WO1981002423A1
WO1981002423A1 PCT/CH1981/000020 CH8100020W WO8102423A1 WO 1981002423 A1 WO1981002423 A1 WO 1981002423A1 CH 8100020 W CH8100020 W CH 8100020W WO 8102423 A1 WO8102423 A1 WO 8102423A1
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Prior art keywords
parts
dyes
dicyandiamide
dyeing
cellulose
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PCT/CH1981/000020
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German (de)
English (en)
Inventor
T Robinson
B Kissling
W Knobel
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Sandoz Ag
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Priority to BR8106870A priority Critical patent/BR8106870A/pt
Publication of WO1981002423A1 publication Critical patent/WO1981002423A1/fr

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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/38—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
    • C08G12/043—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds with at least two compounds covered by more than one of the groups C08G12/06 - C08G12/24
    • C08G12/046—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds with at least two compounds covered by more than one of the groups C08G12/06 - C08G12/24 one being urea or thiourea
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
    • C08G12/043—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds with at least two compounds covered by more than one of the groups C08G12/06 - C08G12/24
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
    • C08G12/34—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds and acyclic or carbocyclic compounds
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
    • D06M15/423—Amino-aldehyde resins
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/52—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing synthetic macromolecular substances
    • D06P1/5264—Macromolecular compounds obtained otherwise than by reactions involving only unsaturated carbon-to-carbon bonds
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/52—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing synthetic macromolecular substances
    • D06P1/56—Condensation products or precondensation products prepared with aldehydes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58—Material containing hydroxyl groups
    • D06P3/60—Natural or regenerated cellulose
    • D06P3/62—Natural or regenerated cellulose using direct dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58—Material containing hydroxyl groups
    • D06P3/60—Natural or regenerated cellulose
    • D06P3/66—Natural or regenerated cellulose using reactive dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/02—After-treatment
    • D06P5/04—After-treatment with organic compounds
    • D06P5/08—After-treatment with organic compounds macromolecular

Definitions

  • the present invention relates to new agents which include can be used to improve the wet fastness of substantive rubbing and printing on cellulose-containing textiles.
  • Dyeing and printing with noun dyes are often insufficient in their water and wash fastness.
  • the dyes superficially bound to the cellulose fiber are gradually removed from the fiber by repeated washing processes. When bleeding into the wash liquor, they can be partially drawn onto undyed cellulose material. There is no shortage of attempts to remedy these disadvantages.
  • examples may be mentioned: complex formation with metal salts on the fiber, diazotization of the dye on the fiber, further formalization of the dye and fiber, and finally impregnation with synthetic resins and the use of cationic aftertreatment agents.
  • the use of cationic aftertreatment agents has proven particularly useful.
  • those substantive dyes also include those cellulose-reactive dyes in which the dye (without reactive component) has substantivity.
  • a disadvantage of dyeing with reactive dyes is the fact that reactive dyeings require an energy-consuming and time-consuming wash to remove the non-chemically bound (saponified) dye portion.
  • the aim according to the invention is accordingly agents which enable a wash-resistant improvement in the wet fastness of direct dyeings, which also withstand repeated washing operations at temperatures between 40-100 ° C., but especially at and above 60 ° C., and which are further able to rinse after reactive dyeings reduce or make completely redundant.
  • the present invention now relates to reaction products of a polycationic amine obtained by condensation of a primary or secondary amine with cyanamide, dicyandiamide, guanidine, bisguanidine or a derivative thereof or from ammonia with cyanamide or dicyandiamide (A) and N-methylol compounds of ureas, melamines, guanamines , Triazones, urones, carbamates or acid amides (B) which are still water-soluble or dispersible and have a viscosity of up to 200 cp as 50-70% aqueous preparations.
  • A ammonia with cyanamide or dicyandiamide
  • B acid amides
  • This invention further relates to the use of these reaction products for dyeing textiles containing or consisting of cellulose fibers in the presence of such catalysts (C) which are used for the crease-resistant finishing of cellulose textiles with the aforementioned methylol compounds, and dyeing auxiliaries which these Contain reaction products and the catalysts (C) mentioned and finally also the textiles which are dyed by means of these reaction products or dyeing aids containing them.
  • Preferred starting materials (A) are the reaction products from one
  • R independently of one another hydrogen or a C 1 -C 11 alkyl group, optionally substituted by a hydroxyl, C 1 -C 4 alkoxy or
  • Cyan group means n is an integer from 1-100, each Z independently of one another when n> 0 is a C 1 -C 4 alkylene or hydroxyalkylene group and X - in the case of n ⁇ 1 independently of one another - one - 0, -S or NR group, where R has the definition given above, with the proviso that the amine of formula Ib contains at least one reactive -NH or -NH 2 group.
  • Reaction products of the polyamines Ib with cyanamide, dicyandiamide or guanidine are particularly preferred, where in the amines Ib R is preferably hydrogen or a C 1 -C 4 -alkyl or hydroxyalkyl radical, each R is particularly preferably hydrogen, n is preferably a number from 0 -30 (fractional values are also possible as an average value), especially from 1-6.
  • Z is preferably ethylene, 1,3-propylene or 1,3- (2-hydroxy) propylene.
  • X is preferably -NR-, especially -NH-.
  • Particularly preferred amines are diethylene triamine or triethylene tetramine and higher polyethylene (or polypropylene or polyhydroxy-propylene) polyamines containing up to 8, preferably up to 6, N atoms.
  • the reaction with cyanamide, dicyandiamide, guanidine or bisguanide can be carried out with the free form of the amine bases or in salt form, e.g. be carried out as carbonates; in the case of ammonia, the reaction as ammonium salt is preferred in any case.
  • Preferred reactants are dicyandiamide or guanidine, preferably the former.
  • Particularly valuable compounds are those made from dicyandiamide with diethylene tri- or triethylene tetramine.
  • the reaction components for the starting material (A) are reacted with one another in the absence of water and in an inert, non-aqueous solvent, preferably without solvent at 140-160 ° C.
  • the reaction proceeds with elimination of ammonia.
  • the molar ratio is generally 0.1 to 1 mol of cyanamide, dicyandiamide, guanidine or bisguanide per molar equivalent of a reactive -NH or -NH - group.
  • the molar ratio is 2: 1 to 1: 2, preferably around 1.
  • the end products are basic syrupy to thick, almost colorless liquids or solid substances that form soluble salts with organic or inorganic acids.
  • the second component of the starting materials of the present invention are generally those N-methylol compounds known as crosslinkers for cellulosic fibers (for finishing). Both acyclic. Cyclic N-methylol compounds, which can also be fatty, are also suitable. Suitable N-methylol compounds are those of the structures mentioned below (the etherified derivatives preferably being C 1 -C 4 -alkyl ethers).
  • Each R 2 is -CH 2 OH or H, at least one and preferably two of the R 2 groups being -CH 2 OH.
  • R 2 has the above meaning
  • R 3 is C 1 -12 -
  • N-methylol compounds are e.g. described in textile finishing 3 No. 8, pp. 414-415 (1968).
  • the precursors are particularly suitable for the hydrolysis-resistant reactant resins, such as the N, N'-dimethylol or N, N'-dialkoxymethyl derivatives of 4,5-dihydroxy- or 4,5-dimethoxyethylene urea, and N, N'-dimethylol or N, N'-dialkoxymethyl derivatives of carbamates. Mixtures of the above-mentioned N-methylol compounds are also suitable. If the compounds are in etherified form, they are preferred
  • the compounds according to the invention are preferably prepared from the products (A) and (B) by adding portions (A), if appropriate in concentrated aqueous solution, into the aqueous solution (preheated to about 60-70 ° C.) of (B) ( preferably as an approx. 50% aqueous solution). Stir until solution.
  • the solutions of the compounds (B) can already contain the (previously dissolved) catalyst (C). The condensation is then carried out until the reaction product obtained has not yet gelled and is still water-soluble or water-dispersible.
  • the reaction temperature in the aforementioned reaction of (A) and (B), which is preferably also carried out with constant stirring, is between room temperature and 80 ° C., preferably at 60-75 ° C.
  • the reaction must be stopped before the reaction product becomes water-insoluble or gelled, the duration of the reaction is between 30 minutes and 3 hours, the end product has a viscosity (at room temperature) between 50 and 200, preferably 60-150 cp. in the composition present from the reaction, i.e. including the water that is present during the reaction, that is ⁇ 30-50% based on the total amount of the end product.
  • reaction product of (A) and (B) can already contain the catalyst (C) during the reaction without interfering with it.
  • The-. ⁇ er can also be added later.
  • the reaction product is stable at room temperature. At slightly elevated temperatures or after standing for a very long time (weeks or months) it can partially or largely lose its activity with the formation of a gel.
  • the technical application of a gel in dyeing technology is disadvantageous, since dosing is difficult.
  • a reaction product can be obtained by adding 1 to 10% (based on the total mixture of A and B) of cyanamide, dicyandiamide or bisguanide, preferably dicyandiamide, which can also be obtained after prolonged standing not gelled and its full effect continues even after weeks and months.
  • the stabilizer, especially dicyandiamide can be added before, during or after the mixture of (A) and (B), preferably before or during the reaction, together with the curing catalyst (C).
  • the reaction product from (A) and (B) reacts with the OH groups of the cellulose by means of the catalysts (C), which are already known as such for the crosslinking of compounds of type (B) in the cellulose. It is e.g.
  • acidic salts of polyvalent metals such as the nitrates, sulfates, chlorides, tetrafluoroborates or hydrogen phosphates of aluminum, magnesium, zinc or zirconium, e.g. Aluminum nitrate, sulfate, chloride or dihydrogen phosphate, magnesium or zinc nitrate, sulfate, chloride or dihydrogen phosphate. Mixtures of such compounds are also suitable, e.g. those made from magnesium chloride, aluminum chloride and aluminum hydroxychloride, from zinc nitrate and aluminum sulfate and others. Other examples are zinc fluoroborate and zirconyl oxychloride.
  • catalysts mentioned above are also suitable in a mixture with neutral inorganic water-soluble salts, in particular with alkali metal sulfates such as sodium sulfate or potassium sulfate or alkaline earth metal salts, especially chlorides, especially calcium.
  • alkali metal sulfates such as sodium sulfate or potassium sulfate or alkaline earth metal salts, especially chlorides, especially calcium.
  • Combinations of acids and salts such as phosphoric acid and ammonium chloride or calcium chloride are also suitable, as are hybrids with organic acids such as citric acid.
  • organic acids such as citric acid.
  • Further examples are sodium bisulfite, the tetrafluoroborates of zinc and magnesium, organic hydrochlorides, for example 2-amino-2-methylpropanol hydrochloride.
  • Organic acids themselves, e.g. Citric acid, oxalic acid, maleic acid, glycolic acid, trichloroacetic acid and inorganic acid such as phosphoric acid, hydrochloric acid can be used, either alone or in combination with metal salts.
  • suitable catalysts are also ammonium salts of inorganic acids, such as ammonium nitrate, chloride, sulfate, mono- and diammonium phosphate, ammonium oxalate and others. Which catalyst is optimally used in the given case largely depends on the choice of the agent from (A) and (B), especially the component (B).
  • Preferred catalysts are the above-mentioned Al, Mg or Zn salts, especially the Mg salts, especially MgCl 2 , optionally together with alkali, especially Na sulfate, the optimal catalyst here also being based on the type of agent used, especially component (B ) depends.
  • these catalysts can already be present in the preparation of the reaction products according to the invention. They must be added later if this is not the case, or they must be added to the liquors before the reaction products are used for the aftertreatment of dyeings.
  • the colors; whose aftertreatment is the subject of the present invention can be applied to any conventional. Be carried out manner known for direct dyeing or dyeing with reactive dyes. They can be carried out both in the exhaust process and in the printing process, furthermore from short as well as from long liquors, in the heat and according to the method of the cold residence process.
  • the aftertreatment according to the invention takes place after the dyeing has been fixed and the dyed textile material can be dried in between or can be aftertreated in the moist state, this being ensured must ensure that there is sufficient penetration of the goods (pick up).
  • the reaction product of (A) and (B) together with the catalyst (C) can be applied to the substrate in a known manner, in the padding process, such as by plopping, spraying, dipping, in foam application and similar application processes, preferably at room temperature.
  • agents according to the invention are used largely depend on the depth of color of the dyeings to be fixed. For stains e.g. 1/1 standard strength, these amounts are 30-200 g / 1 impregnation liquor, preferably 70-130 g / 1 for cotton and 100-200 g / 1 for regenerated cellulose, with a squeezing effect after impregnation of approx. 70-100% ( based on dry weight).
  • the fixation takes place according to one of the known dry crosslinking methods; After impregnation and squeezing, the pre-drying and condensing can be carried out in one operation at temperatures between 120-200 ° C, especially 130-180 ° C, for example, either by a shock drying process. You can also pre-dry at temperatures of 70-120 ° C and then at temperatures of 120-200 ° C, preferably 140-180 ° C for 5 seconds to 8 minutes, preferably 30 seconds to 1 minute, at 170- Network at 180 ° C.
  • cellulose fibers e.g. Cotton and viscose
  • their blended fabrics can also be treated according to the invention with e.g. synthetic fibers if they have been dyed with direct or reactive dyes.
  • the amount used is to be calculated on the cellulose content.
  • the amount of the reaction product according to the invention to be used largely depends on the amount of the unfixed dye portion. This portion of the dye is so firmly and wash-bound by the aftertreatment that an energy-consuming and time-consuming wash of the reactively dyed textile goods can be largely or completely dispensed with.
  • Direct dyes are particularly suitable for the dyeing process according to the invention with the agents according to the invention, and of these the metal complex dyes, especially the copper complexes.
  • the Rf value can be used for a given reaction product of the type according to the invention.
  • Dyes which have an Rf value of ⁇ 0.35 at room temperature (20-25 ° C) are generally suitable for a reaction product from the dicysndiamide / diethylenetriamine reaction with dimethylol-dihydroxyethylene urea (of the type of Example 1).
  • the thin-layer chromatogram is prepared using a freshly prepared mixture of the abovementioned composition on 0.25 mm silica gel with a fluorescence indicator (Polygram SIL g / UV 254). As dyes, those that are available as commercial products are tested (in their respective settings).
  • Dyes with 3-4 sulfonic acid groups which belong to the class of so-called “small molecules” (MW ⁇ 900), are generally less suitable - even if their Rf value is ⁇ 0.35.
  • a further, more general test method for determining the aid according to the invention which is most suitable for a given dye consists in the following experimental arrangement: dye and the precursor of the cationic aid [which has not yet been used with the Reactant resin (N-methylol compound) has been reacted] and must precipitate as an insoluble precipitate. After washing the precipitate, it must not redissolve in alkaline solution at pH 12.
  • Both of the aforementioned tests are valuable for the dyeing technician in order to be able to quickly and safely make a dye selection or to be able to determine whether the dye can be improved in terms of its properties with a certain canonical aid in such a way that it can be used practically.
  • wash-resistant improvements in wet fastness of direct dyeings and prints on cellulose textiles which can be achieved with the compounds according to the invention are also stable in the case of repeated alkaline washes at temperatures between 40-80 ° C., especially at and above 60 ° C. Wash liquors (liquor e.g. 1:50) with z.3. 5 g / 1 soap and 2 g / 1 soda calc. and repeated washes of 30 minutes each are easily tolerated. Pure cellulose of all common types, as well as blended fabrics of cellulose fibers with other native or synthetic fibers can be dyed true to color with direct dyes. The dyeings are further characterized by good light fastness.
  • reaction product obtained can be used as such for the purpose according to the invention (together with a curing catalyst, for example magnesium chloride). This can also be added during the above-described reaction (15 parts of magnesium chloride hexahydrate).
  • a reaction product which is stable over a long period of time is obtained if the procedure of Example 2 is followed, but in the 50% range Dirnethyloldihydroxy-ethylene urea solution before the addition of the first-mentioned reaction product together with or after the magnesium chloride hexahydrate addition, 5 parts of dicyandiamide are added and then allowed to react at 79 ° for 2-3 hours.
  • Example 6 50 parts of the suspension obtained are neutralized with 14.8 parts of 90% sulfuric acid. After adding 15 parts. Magnesium chloride hexahydrate and 100 parts of a 50% aqueous solution of dimethyloldihydroxyethylene urea is allowed to react at 70 ° for about 1 hour. A cloudy, water-soluble liquid is created which can be used as such.
  • Example 6 50 parts of the suspension obtained are neutralized with 14.8 parts of 90% sulfuric acid. After adding 15 parts. Magnesium chloride hexahydrate and 100 parts of a 50% aqueous solution of dimethyloldihydroxyethylene urea is allowed to react at 70 ° for about 1 hour. A cloudy, water-soluble liquid is created which can be used as such.
  • Example 6 50 parts of the suspension obtained are neutralized with 14.8 parts of 90% sulfuric acid. After adding 15 parts. Magnesium chloride hexahydrate and 100 parts of a 50% aqueous solution of dimethyloldihydroxyethylene urea is allowed to react at 70 ° for about 1 hour.
  • the reaction is exothermic and the temperature rises from room temperature to 40 °. After the exothermic reaction has ended, the temperature is kept at 40 ° for one hour. A clear, yellow liquid is obtained which can be used as such or after further dilution.
  • Example (7) 25 parts of the dicyandiamide / tetraethylene pentamine condensation product obtained in Example (7) are dissolved in 200 parts of water and neutralized with a 35% strength aqueous hydrochloric acid solution. At 50 ° and 25 Torr, water is distilled off until 110 parts of a concentrated solution of the neutralized condensation Product. This is then mixed with 100 parts of an 80% aqueous solution of hexamethylolmelamine for 2 hours. A cloudy, water-soluble liquid is obtained which can be used as such.
  • Example 2 30 parts of this powder are reacted in 100 parts of a 50% aqueous solution of 20 parts of dimethylol urone and 25 parts of dinethyloldihydroxyethylene urea according to the conditions of Example (2). 20 parts of magnesium chloride hexahydrate are stirred in beforehand. A reaction product having the properties of Example (2) is obtained.
  • Example 12 51.5 parts of diethylene triamine are heated to 130 ° with 45 parts of guanidine carbonate and then left to react for 5 hours at 140-150 °. The reaction product is pulverized. 30 parts of this reaction product are further reacted according to the information in Example (2), a reaction product being obtained which can be used as such.
  • Example 12 51.5 parts of diethylene triamine are heated to 130 ° with 45 parts of guanidine carbonate and then left to react for 5 hours at 140-150 °. The reaction product is pulverized. 30 parts of this reaction product are further reacted according to the information in Example (2), a reaction product being obtained which can be used as such.
  • Example 12 51.5 parts of diethylene triamine are heated to 130 ° with 45 parts of guanidine carbonate and then left to react for 5 hours at 140-150 °. The reaction product is pulverized. 30 parts of this reaction product are further reacted according to the information in Example (2), a reaction product being obtained which can be used as such.
  • Example 2 130 parts of diethylene triamine and 42 parts of cyanamide are heated to 110-140 ° for 6 hours.
  • the reaction product obtained is neutralized with sulfuric acid (with cooling) and spray-dried.
  • the further implementation takes place according to the information in Example 2, a product being obtained which has the same properties as that of Example 2.
  • a cotton dyeing with the dye of formula VII (standard depth 1/1) is impregnated with a solution containing 100 g / 1 of the product according to example (1) on a padder and squeezed to a liquor intake of about 80%. It is then shock-dried on a tenter at a temperature of 175-180 ° in such a way that the pure condensation time of the dry tissue is approximately 30-45 seconds.
  • the fixed blue color is characterized by a high fastness to washing, which maintains its good fastness properties even after repeated 60 ° washes and even withstands boiling. At the same time, a significant improvement in the creasing rate is achieved and the swelling value of the cellulose fiber is reduced.
  • a cotton dyeing with 3% of the dye of formula VIII is prepared with 80 g / l of a solution according to example (2) according to the instructions in example (13)
  • a dyeing with 2.4% of the dye of formula V is aftertreated as described in Example (13) with the agent according to Example (10).
  • a rinsed dry cotton pull-out dyeing is impregnated on a padding machine with a solution which contains the fixing agent (1) and, if appropriate, additionally the specified amount of magnesium chloride hexahydrate (2) and to a liquor absorption of approximately 80%. squeezed.
  • the means used are shown in the table below.
  • a solution containing 130 g / 1 of the product of Example (1) is padded onto a cotton fabric and then squeezed to a liquor absorption of approximately 80%.
  • the liquor contains plasticizers and wetting agents, namely 10 g / 1 of an anionic commercial plasticizer (with 20 g / 1 of a polyethylene dispersion) and 1 g / 1 of a non-ionic commercial wetting agent.
  • the tissue After squeezing, the tissue is dried to a 2-4% residual moisture and then condensed at 180 ° for 30-45 seconds.
  • the coloring fixed in this way is characterized by a high fastness to washing, which is retained despite inadequate washing. At the same time, a clear improvement in the crease resistance is achieved.

Abstract

Les produits de reaction d'amines primaires ou secondaires ou de polyamines avec le cyanamide, le dicyanamide, la guanidine ou u n de leurs derives ou de l'ammoniaque avec le cyanamide ou dicyanamide (A) sont mis en presence de composes N-methylol d'urees, de melamines, traizones, urones, carbamates ou d'acideamides (B). On obtient ainsi des composes pour l'amelioration de la resistance au mouille lors de coloration avec des colorants directs de textiles composes de fibres de cellulose ou a base de telles fibres. Ces composes sont appropries pour la fixation d'un colorant reactif non lie dans des colorations avec ce type de colorant.
PCT/CH1981/000020 1980-02-22 1981-02-19 Moyens de coloration et procede pour la coloration de fibres cellulosiques WO1981002423A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
BR8106870A BR8106870A (pt) 1980-02-22 1981-02-19 Agente auxiliar de tingimento e processo para o tingimento de fibras celulosicas

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
CH143680 1980-02-22
CH1436/80 1980-02-22
DE3035893 1980-09-24
DE3035942 1980-09-24
DE3044441 1980-11-26

Publications (1)

Publication Number Publication Date
WO1981002423A1 true WO1981002423A1 (fr) 1981-09-03

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PCT/CH1981/000020 WO1981002423A1 (fr) 1980-02-22 1981-02-19 Moyens de coloration et procede pour la coloration de fibres cellulosiques

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US (1) US4410652A (fr)
KR (1) KR840001155B1 (fr)
AT (1) AT398315B (fr)
AU (1) AU546008B2 (fr)
BR (1) BR8106870A (fr)
CA (1) CA1177184A (fr)
CH (1) CH662919GA3 (fr)
ES (1) ES499663A0 (fr)
FR (1) FR2476670A1 (fr)
GB (1) GB2070006B (fr)
HK (1) HK83684A (fr)
IT (1) IT1170738B (fr)
MY (1) MY8500800A (fr)
NL (1) NL187688C (fr)
SG (1) SG54084G (fr)
WO (1) WO1981002423A1 (fr)

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EP0286597A2 (fr) * 1987-04-06 1988-10-12 Sandoz Ag Teinture et impression de fibres
CH669305GA3 (fr) * 1981-12-11 1989-03-15
CH669705GA3 (fr) * 1982-08-30 1989-04-14
FR2626903A1 (fr) * 1988-02-08 1989-08-11 Sandoz Sa Procede de teinture de substrats mixtes
DE3938918A1 (de) * 1989-11-24 1991-05-29 Sandoz Ag Mischungen mit synergistischen eigenschaften
WO1998038378A1 (fr) * 1997-02-26 1998-09-03 Textilcolor Ag Compose polymere a faible poids moleculaire, modifie avec du carbamate, et son utilisation pour le traitement ulterieur de materiau textile a base de cellulose, teint ou imprime
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JP2000219511A (ja) * 1999-01-28 2000-08-08 Nippon Carbide Ind Co Inc シアナミド水溶液
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BRPI0418218A (pt) * 2003-12-29 2007-04-27 Clariant Finance Bvi Ltd tratamento posterior de tinturas têxteis ou estampas em cores
WO2011079041A1 (fr) 2009-12-24 2011-06-30 Novomer, Inc. Procédés pour la synthèse de composés de guanidine polycycliques
HRP20230961T1 (hr) * 2019-09-18 2023-12-08 Georg-August-Universität Göttingen Stiftung Öffentlichen Rechts Modificirano drvo

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DE907164C (de) * 1950-08-09 1954-03-22 Ciba Geigy Verfahren zur Verbesserung der Nassechtheiten von Faerbungen und Drucken und Faerbepraeparate
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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH669305GA3 (fr) * 1981-12-11 1989-03-15
CH669705GA3 (fr) * 1982-08-30 1989-04-14
DE3505018A1 (de) * 1984-02-24 1985-09-05 Sandoz-Patent-GmbH, 7850 Lörrach Nachbehandlungsverfahren fuer gefaerbtes textilmaterial
DE3533383A1 (de) * 1984-09-29 1986-04-03 Sandoz-Patent-GmbH, 7850 Lörrach Faerbeverfahren
EP0286597A2 (fr) * 1987-04-06 1988-10-12 Sandoz Ag Teinture et impression de fibres
EP0286597A3 (en) * 1987-04-06 1989-11-23 Sandoz Ag Dyeing and printing fibres
FR2626903A1 (fr) * 1988-02-08 1989-08-11 Sandoz Sa Procede de teinture de substrats mixtes
DE3938918A1 (de) * 1989-11-24 1991-05-29 Sandoz Ag Mischungen mit synergistischen eigenschaften
DE19734062B4 (de) * 1996-10-09 2006-04-13 Fuji Spinning Co., Ltd. Verfahren zum Färben und Veredeln von Textilerzeugnissen, die modifizierte Zelluloseregeneratfaser enthalten
WO1998038378A1 (fr) * 1997-02-26 1998-09-03 Textilcolor Ag Compose polymere a faible poids moleculaire, modifie avec du carbamate, et son utilisation pour le traitement ulterieur de materiau textile a base de cellulose, teint ou imprime
US6844428B2 (en) 2000-12-04 2005-01-18 Clariant Finance (Bvi) Limited Use of disazo compounds

Also Published As

Publication number Publication date
NL187688C (nl) 1991-12-16
SG54084G (en) 1985-03-08
GB2070006A (en) 1981-09-03
BR8106870A (pt) 1981-12-22
HK83684A (en) 1984-11-09
ES8206703A1 (es) 1982-08-16
CH662919GA3 (en) 1987-11-13
FR2476670A1 (fr) 1981-08-28
US4410652A (en) 1983-10-18
IT8147849A0 (it) 1981-02-20
AU6751481A (en) 1981-08-27
ATA77681A (de) 1994-03-15
KR830005427A (ko) 1983-08-13
AU546008B2 (en) 1985-08-08
GB2070006B (en) 1984-05-02
NL8100795A (nl) 1981-09-16
KR840001155B1 (ko) 1984-08-11
FR2476670B1 (fr) 1984-07-20
IT1170738B (it) 1987-06-03
ES499663A0 (es) 1982-08-16
NL187688B (nl) 1991-07-16
AT398315B (de) 1994-11-25
CA1177184A (fr) 1984-10-30
MY8500800A (en) 1985-12-31

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